Brattleboro, VT Homes

• 

  

  

  /34

  Est $552,856 Not Listed For Sale

  • 2 Beds
  • 3 Baths
  • 2,500 Sq Ft

  1245 Black Mountain Rd, Brattleboro, VT 05301

  1245 Black Mountain Rd, Brattleboro, VT 05301
• 

  

  

  /19

  $84,500

  • 3 Beds
  • 1 Bath
  • 1,490 Sq Ft

  7 Nichols Dr, Guilford, VT 05301

  This two story home offers 3 bedrooms/1 bathroom with 1,490 sq. ft. of living space. The property sits on a 0.50 acre lot. The first floor has a kitchen with wooden cabinets and granite countertops, wood flooring and a carpeted living room. A dedicated laundry area is also included. The property features a barn in the backyard for storage. Exterior highlights include a covered front entry,

  Derek Greene Derek Greene

  7 Nichols Dr, Guilford, VT 05301
• 

  

  

  /38

  $239,000 Sold Aug 14, 2025

  • 1,056 Sq Ft
  • $226/SF
  • 13 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1988

  81 Morningside Commons, Guilford, VT 05301

  The moment you step into this condo, you notice its unique features and feel a sense of calm. In the living room, you’ll enjoy the “Anywhere” ethanol fireplace for its ambience and extra heat - with no connections, venting or emissions to worry about! The kitchen has been carefully redone, with expanded cabinetry and improvements to the layout and lighting, including a custom display cabinet and

  Victoria Woods Brattleboro Area Realty

  81 Morningside Commons, Guilford, VT 05301
• 

  

  

  /22

  Est $303,366 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  1075 Middle Rd, Brattleboro, VT 05301

  1075 Middle Rd, Brattleboro, VT 05301
• 

  

  

  /24

  $279,000

  • 3 Beds
  • 1 Bath
  • 912 Sq Ft

  91 Carriage Hill Rd, Brattleboro, VT 05301

  This charming split-level home offers 3 bedrooms and a full bathroom, complete with a single-bay garage in the desirable Carriage Hill neighborhood. Hardwood floors extend through the living room, hall, and bedrooms, adding warmth and character. The living room features a lovely picture window with opening side windows, perfect for letting in a refreshing breeze and natural light.The lower level

  Rebecca Seymour Brattleboro Area Realty

  91 Carriage Hill Rd, Brattleboro, VT 05301
• 

  

  /39

  $329,000 Sold Aug 14, 2025

  • 1,713 Sq Ft
  • $192/SF
  • 24 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1920

  158 Clark Ave, Brattleboro, VT 05301

  Lovingly refurbished and full of timeless charm, this two bedroom, one bathroom Arts and Crafts bungalow offers bright, comfortable living within a mile from Brattleboro Memorial Hospital and both the middle and high schools. Set on a beautifully level lot, the home features a welcoming enclosed porch, a covered outdoor dining area perfect for three-season enjoyment, and a built-in one-car garage

  Andie Fusco Four Seasons Sotheby's Int'l Realty

  158 Clark Ave, Brattleboro, VT 05301
• 

  

  /12

  Est $227,000 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 924 Sq Ft

  129 West St, Brattleboro, VT 05301

  129 West St, Brattleboro, VT 05301
• 

  

  /37

  $849,000

  • 4 Beds
  • 4 Baths
  • 3,600 Sq Ft

  5 Hillwinds N, Brattleboro, VT 05301

  Elegant Post-and-Beam home in coveted Hillwinds. Tucked along a birch-lined drive, this exceptional post-and-beam home is set on 11+ acres of landscaped grounds with lawns, stone walls, gardens, and mixed woodland in the desirable Hillwinds community. Enjoy direct trail access and easy proximity to downtown and the Country Club. Step inside the striking custom-designed interior through a covered

  Robert Doyle Berkley & Veller Greenwood Country

  5 Hillwinds N, Brattleboro, VT 05301
• 

  

  /46

  $668,000 Sold Aug 12, 2025

  • 2,226 Sq Ft
  • $300/SF
  • 7 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1985

  395 Hillwinds Rd, Brattleboro, VT 05301

  Turnkey Home in Sought-After Hillwinds! Located in the desirable Hillwinds neighborhood and nestled among the trees, your dream home awaits! This charming and functional home offers open, sun-filled living spaces, softwood floors, and abundant storage. The kitchen is a cook’s dream, featuring granite countertops, a gas stove, farmhouse sink, and a unique pull-out cabinet on wheels for added

  Desiree Stango Berkley & Veller Greenwood Country

  395 Hillwinds Rd, Brattleboro, VT 05301
• 

  

  /40

  Est $363,194 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,716 Sq Ft

  36 Goldfinch Ln, Brattleboro, VT 05301

  36 Goldfinch Ln, Brattleboro, VT 05301
• 

  

  /38

  $549,900

  • 3 Beds
  • 2 Baths
  • 2,476 Sq Ft

  458 Bonnyvale Rd, Brattleboro, VT 05301

  PRICE REDUCTION! THE 4.875 ACRE LOT NEXT DOOR HAS BEEN REMOVED FROM SALE. Welcome to this inviting West Brattleboro home, perfectly situated just 1 mile from Route 9 and 2 miles from I-91 on 1.95 private acres. Relax by the in-ground pool, soak in the jacuzzi tub, or enjoy your own blueberry bushes, raspberry bushes, and beautifully maintained flower and vegetable gardens. Recent updates include

  Kelsea McAuliffe Greenwald Realty Group

  458 Bonnyvale Rd, Brattleboro, VT 05301
• 

  

  /28

  $180,000 Sold Aug 12, 2025

  • 1,531 Sq Ft
  • $118/SF
  • 70 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1941

  316 Putney Rd, Brattleboro, VT 05301

  Convenient Location & Low Maintenance Living! Enjoy easy access to shopping, public transportation and waterfront with scenic trails. The backyard is just the right size for enjoying nature and a little fresh air. This charming home combines classic character with practical updates featuring a standing seam roof, vinyl windows and aluminum siding. Inside, the home radiates its original charm

  Kristen Ziter Taylor Brattleboro Area Realty

  316 Putney Rd, Brattleboro, VT 05301
• 

  

  /32

  Est $328,271 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft

  499 S Main St, Brattleboro, VT 05301

  499 S Main St, Brattleboro, VT 05301
• 

  

  /29

  $345,000

  • 4 Beds
  • 2 Baths
  • 2,408 Sq Ft

  78-80 Central St, Brattleboro, VT 05301

  Charming Two-Unit Multi-Family on Quiet In-Town Street – Ideal for Investors or Owner-Occupants! Tucked away on a peaceful side street yet just minutes from shopping, dining, and public transportation, this two-family property offers the perfect blend of convenience and comfort. The current owners have updated all the electrical in both units. Each unit features spacious, light-filled

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  78-80 Central St, Brattleboro, VT 05301
• 

  

  /22

  $336,000 Sold Aug 12, 2025

  • 1,104 Sq Ft
  • $304/SF
  • 63 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1968

  62 Lawton Dr, Brattleboro, VT 05301

  Everything deserves a second chance, and this home found the right owner to love and recreate it in a stunning new life. Anyone who has looked at this home in the past few years, has to come back to see the shine....the fresh new look....the simplicity of move right in. Not only is this home refreshed stem to stern, it has new windows, siding, shingles, kitchen, bath.....and on and on! Tuck

  Christine Lewis Brattleboro Area Realty

  62 Lawton Dr, Brattleboro, VT 05301
• 

  

  /27

  Est $200,337 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,665 Sq Ft

  379 S Main St, Brattleboro, VT 05301

  379 S Main St, Brattleboro, VT 05301
• 

  

  /58

  $568,000

  • 3 Beds
  • 2 Baths
  • 2,066 Sq Ft

  192 Western Ave, Brattleboro, VT 05301

  Timeless 1855 classic with historic charm just minutes to downtown Brattleboro. Step back in time with this beautifully preserved home, offering a rare blend of vintage character and modern comfort. Featuring three bedrooms and two bathrooms, this home is perfect for those who appreciate craftsmanship and history. Thoughtful updates complement the historic features without compromising

  Claire Renaud Berkley & Veller Greenwood Country

  192 Western Ave, Brattleboro, VT 05301
• 

  

  /5

  $100,000 Sold Aug 11, 2025

  • 700 Sq Ft
  • $143/SF
  • 19 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1966

  39 Brookside Dr Unit 7, Brattleboro, VT 05301

  Ready for a redo, this home is priced right for anyone who is handy with freshening, light carpentry (flooring) and other minor skills. Worth the effort to find an affordable option to renting or living with Mom! 48 hour a must for notice. This condo is located in a prime location with quick, easy access to I91 and a stones throw to the Whetstone Brook, Farmers Market and Living Memorial Park.

  Christine Lewis Brattleboro Area Realty

  39 Brookside Dr Unit 7, Brattleboro, VT 05301
• 

  

  /23

  Est $287,464 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,539 Sq Ft

  380 S Main St, Brattleboro, VT 05301

  380 S Main St, Brattleboro, VT 05301
• 

  

  /25

  $189,000

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft

  22 Chestnut St Unit 1, Brattleboro, VT 05301

  Welcome to 22 Chestnut Street, Unit #1 — a charming and fully furnished first-floor condo nestled in the lovely Chestnut Street neighborhood. This spacious 2-bedroom, 1-bath unit features a thoughtfully updated bathroom with a clawfoot tub and separate shower, a cozy mudroom entryway, and a sunny side porch that conveys with the unit — perfect for morning coffee or evening relaxation. The kitchen

  Erica Reynolds Southern Vermont Realty Group

  22 Chestnut St Unit 1, Brattleboro, VT 05301
• 

  

  /59

  $543,000 Sold Aug 07, 2025

  • 5,850 Sq Ft
  • $93/SF
  • 20 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2000

  628 S Main St, Brattleboro, VT 05301

  Absolutely Gorgeous In-Town Home with Exceptional Attention to Detail.This stunning residence offers over 5,000 square feet of meticulously designed living space in the main house, plus a fully separate accessory dwelling with two independent living areas—ideal for extended family, guests, or producing income. Additionally there is a two-car garage with an integrated service pit for

  Kerry Mulverhill

  628 S Main St, Brattleboro, VT 05301
• 

  

  /12

  Est $358,744 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,840 Sq Ft

  71 Home St, Brattleboro, VT 05301

  71 Home St, Brattleboro, VT 05301
• 

  

  /20

  $279,900

  • 4 Beds
  • 2 Baths
  • 1,733 Sq Ft

  1177 Western Ave, Brattleboro, VT 05301

  So much to offer! This 4 bedroom 2 bath has plenty of room for all! It features a large kitchen with lots of counter space and the laundry tucked in for easy access while you cook and bake. The deck overlooks the lower yard where the solar panels live and the perfect spot for the above ground swimming pool (needs a liner). Huge lot, lots of off street parking and on the MOOVER line for non

  Christine Lewis Brattleboro Area Realty

  1177 Western Ave, Brattleboro, VT 05301
• 

  

  /30

  $330,000 Sold Aug 07, 2025

  • 2,146 Sq Ft
  • $154/SF
  • 56 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1952

  116 Edward Heights, Brattleboro, VT 05301

  This spacious, single-level home is neatly tucked away on a large corner lot at the end of the street - no through-traffic! The interior features inviting, open living space on one end and separate rooms at the other, including a walk-in pantry, laundry room and bathroom with a step-in tub. The expansive yard offers both sun and shade, with a screened-in outbuilding (formerly a pool house) and a

  Stephanie Wilde

  116 Edward Heights, Brattleboro, VT 05301
• 

  

  /16

  Est $417,249 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,722 Sq Ft

  68 Wilsons Woods Rd, Brattleboro, VT 05301

  68 Wilsons Woods Rd, Brattleboro, VT 05301
• 

  /2

  $300,000

  • 4 Beds
  • 2 Baths
  • 1,808 Sq Ft

  109 Central St, Brattleboro, VT 05301

  Bright Sunny, south facing! 2 stacked flats just perfect for multi generational living! Inside access with both formal front stair and back utility stairs, so easy for caring for family members, or a plan for aging in place with a care giver. Rent one or both for a money maker. This owner is owner occupying both flats. Plenty of off street parking, a sweet side porch and just a bit of a yard

  Christine Lewis Brattleboro Area Realty

  109 Central St, Brattleboro, VT 05301
• 

  

  /20

  $490,000 Sold Aug 07, 2025

  • 2,400 Sq Ft
  • $204/SF
  • 52 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1880

  21 Howard St, Brattleboro, VT 05301

  This beautiful Victorian home is just a short stroll from vibrant Brattleboro and has access to a huge town trail network. Nicely landscaped and has a partially fenced yard for pets or children. The house has lovely Victorian detailing and includes 3 covered porches. The formal entry has hardwood flooring, period staircase, stained glass window and a 3/4 bath. The adjacent front parlor includes

  Robert Doyle Berkley & Veller Greenwood Country

  21 Howard St, Brattleboro, VT 05301
• 

  

  /40

  Est $469,471 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 1,444 Sq Ft

  67 Wilsons Woods Rd, Brattleboro, VT 05301

  67 Wilsons Woods Rd, Brattleboro, VT 05301
• 

  

  /30

  $579,000

  • 4 Beds
  • 2 Baths
  • 2,656 Sq Ft

  204 Meeting House Ln, Brattleboro, VT 05301

  Your Dream Home Awaits on Meetinghouse Lane! Nestled in the desirable and quiet neighborhood of Meetinghouse Lane, this contemporary home offers both privacy & charm. Surrounded by mature trees, the property feels like a peaceful retreat, while still being conveniently located. A paved driveway leads to an oversized two-car garage, connected to the house by a convenient breezeway. The expansive

  Desiree Stango Berkley & Veller Greenwood Country

  204 Meeting House Ln, Brattleboro, VT 05301
• 

  

  /8

  $165,000 Sold Aug 06, 2025

  • Land
  • 18.3 Acres
  • $9,016 per Acre

  • 4 Days On Market

  0 Gibson Rd, Brattleboro, VT 05301

  This just doesn't happen, a large parcel,18+ acres, in a desirable Brattleboro location. Just up the road the Brattleboro Country Club. Here you'll find stonewalls, small, intriguing streams and mature hard and softwoods. It's the pine trees, however that take center stage, some of them stretching up over 100 feet. If the acreage isn't quite enough there's an adjacent parcel on the market as

  Bill Hickok Berkley & Veller Greenwood Country

  0 Gibson Rd, Brattleboro, VT 05301
• 

  

  /30

  Est $391,397 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,719 Sq Ft

  49 Marlboro Ave, Brattleboro, VT 05301

  49 Marlboro Ave, Brattleboro, VT 05301
• 

  /2

  $89,000

  • 4 Beds
  • 3 Baths
  • 2,108 Sq Ft

  321 Williams St, Brattleboro, VT 05301

  Great opportunity for starting or expanding your investment portfolio. Good rental income and affordable property. Nice location. Good parking for tenants and private porches. Minimal yard maintenance.

  Susan Bellville Bellville Realty

  321 Williams St, Brattleboro, VT 05301
• 

  

  /19

  $305,000 Sold Aug 05, 2025

  • 1,500 Sq Ft
  • $203/SF
  • 41 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1950

  85 Crosby St, Brattleboro, VT 05301

  Charming 1950s Gem! Step into timeless warmth and character with this delightful 3-bedroom, 1-bath home. This lovingly cared for home features beautiful rock maple hardwood floors, solid wood doors, and rich original woodwork that speak to its enduring craftsmanship. Recent updates blend vintage charm with modern comfort, including fresh interior and exterior paint, standing seam metal roof,

  Karen Hoppe Berkley & Veller Greenwood Country

  85 Crosby St, Brattleboro, VT 05301
• 

  

  /24

  Est $546,029 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,592 Sq Ft

  89 Oak Grove Ave, Brattleboro, VT 05301

  89 Oak Grove Ave, Brattleboro, VT 05301
• 

  

  /60

  $549,000

  • 3 Beds
  • 2.5 Baths
  • 3,415 Sq Ft

  23 Meeting House Ln, Brattleboro, VT 05301

  First Time on the Market – Premier Brattleboro Location!Nestled on one of the most desirable lots in one of Brattleboro’s finest neighborhoods, this well-maintained home is being offered for sale for the very first time! Custom-built by the current owner in 1970 with attention to detail, this spacious ranch offers comfort, functionality, and an impressive list of amenities.Perfect for

  Bert Inman RE/MAX Town & Country

  23 Meeting House Ln, Brattleboro, VT 05301
• 

  

  /34

  $334,500 Sold Aug 01, 2025

  • 1,848 Sq Ft
  • $181/SF
  • 57 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1984

  49 Hampshire Cir, Brattleboro, VT 05301

  Cute home at the end of the cul-de-sac. Large front deck with a slider that leads into a newly refinished kitchen, dining area and living room. A half bath with laundry complete the first floor. Two bedrooms upstairs with a full bath. First floor has a door that leads out back to another large deck. The third bedroom and family room in the walkout basement. Open house Saturday 6/21/25 from

  Darlene Conca Keller Williams Realty Metro-Keene

  49 Hampshire Cir, Brattleboro, VT 05301
• 

  

  /14

  Est $319,930 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,492 Sq Ft

  131 Oak Grove Ave, Brattleboro, VT 05301

  131 Oak Grove Ave, Brattleboro, VT 05301
• 

  

  /10

  $175,000

  • Land
  • 8 Acres
  • $21,875 per Acre

  680 W River Rd, Brattleboro, VT 05301

  8 acres only 2 miles from Brattleboro situated across the road from the West River. Existing gated gravel driveway is in. Gravel on site and road roughed into a high plateau with designs for SIX 1-2 bedroom cottages. Topographical survey, septic design plans and other existing engineering are complete which make this an attractive option for someone looking to develop a parcel into a cottage

  Chris Long BHG Masiello Brattleboro

  680 W River Rd, Brattleboro, VT 05301
• 

  

  /9

  $175,000 Sold Jul 31, 2025

  • Land
  • 13.78 Acres
  • $12,700 per Acre

  • 7 Days On Market

  0 E Orchard St Unit 5046918, Brattleboro, VT 05301

  Here's an excellent opportunity to have a larger parcel of land, 13+ acres, in Brattleboro, not only in town but right across the street from the Brattleboro Country Club! This property has not been available for over 35 years and now it's ready for your building plans. This wooded lot features a mature mix of hard and softwoods including some true giants. There's a stream coursing through it

  Bill Hickok Berkley & Veller Greenwood Country

  0 E Orchard St Unit 5046918, Brattleboro, VT 05301
• 

  

  /16

  Est $226,887 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,343 Sq Ft

  23 Winter Ct, Brattleboro, VT 05301

  23 Winter Ct, Brattleboro, VT 05301

Showing Results 41 - 80, Page 2 of 18